Ledbetter and Lomax set out on an arduous journey to record in Arkansas, Alabama, Georgia, South Carolina, North Carolina, and Texas – primarily on prison farms overwhelmingly holding Black prisoners. Ledbetter learns some tunes for which he will later become famous, including “The Rock Island Line.” The strain of their grossly unequal relationship wears Ledbetter down, even as Lomax’s hopes to present the performer to northern audiences build. This chapter explores Ledbetter’s musical aspirations, from his early years as a child prodigy to his time in the Dallas area with Blind Lemon Jefferson.